90358-16-0

Upstream product

• 65062-57-9 2-Amino-5-methyl-3H-pyrrolo<2,3-d>pyrimidin-4(7H)-on 

Downstream Products

• 193891-16-6 4-chloro-7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 90373-55-0 2-Amino-7-<2-desoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-4-methoxy-5-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 90358-18-2 2-Amino-7-<2-desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-methoxy-5-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 181480-52-4 2-Amino-7-benzyl-3,5-dimethyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 181480-49-9 2-Amino-7-benzyl-5-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 183194-48-1 Succinic acid mono-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-5-methyl-4-oxo-3,4-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydro-furan-3-yl] ester 
• 174463-02-6 N-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-isobutyramide 

Relevant academic research and scientific papers

The synthesis and determination of acidic ionization constants of certain 5-substituted 2-aminopyrrolo[2,3-d]pyrimidin-4-ones and methylated analogs

The acidic ionization constants were determined for a series of 5-substituted 2-aminopyrrolo[2,3-dl-pyrimidin-4-ones and N-3- and N-7-methylated analogs thereof. The syntheses of the methylated analogs are also described.

Synthesis and Furanoside/Pyranoside Isomerization of 7-Deaza-2'-deoxy-7-methylguanosine

7-Deaza-2'-deoxy-methylguanosine (2), an isoster of the zwitterionic 2'-deoxy-7-methylguanosine (1) and its α anomer 10b was synthesized.Phase-transfer glycosylation of 2-amino-4-methoxy-5-methyl-7H-pyrrolopyrimidine (6b) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (7a) caused regioselective glycosylation of position 7 to give the anomers 8 and 9 in 87percent yield.Deprotection of the sugar moiety by sodium methanolate gave the nucleosides 10a and 11; subsequent cleavage of the 4-methoxy group by aluminium chloride in DMF leads to 2 and its α anomer 10b.Treatment of 10a with 7 N HCl/dioxane resulted in isomerization and demethylation forming the furanosides 10b and 2 and the pyranosides 12b and 13b.Isomerization of 10a without demethylation was achieved with 1 N hydrochloric acid and gave the furanosides 10a and 11 as well as the pyranosides 12a and 13a.